1-t-Butoxycarbonyl-4-(3-(3,5-difluorophenyl)prop-2-enyl) piperidine → 1-t-Butoxycarbonyl-4-(3-(3,5-difluorophenyl)propyl) piperidine

HRID 1386744Notes

Reaction equation

HRID 1386744 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[CH:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([F:24])[CH:20]=[C:21]([F:23])[CH:22]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 536744281-t-Butoxycarbonyl-4-(3-(3,5-difluorophenyl)prop-2-enyl) piperidine

Product 1

HCID 211806591-t-Butoxycarbonyl-4-(3-(3,5-difluorophenyl)propyl) piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-t-butoxycarbonyl-4-(3-(3,5-difluorophenyl) prop-2-enyl)piperidine (from EXAMPLE 95, Step C) and 50 mg of 10% palladium on carbon in MeOH (10 mL) was hydrogenated at 50 psi for 2 h. The suspension was filtered though Celite, the cake washed with MeOH and the filtrate was concentrated. Flash chomatography using 0-15% EtOAc in hexanes (v/v) as the eluant afforded the title compound: 1H NMR (500 MHz ) δ 1.10 (dq, J=4.4, 8.2, 21), 1.25-1.30 (21), 1.37-1.45 (m, 1H), 1.47 (s, 9H), 1.62-1.67 (4H). 2.59 (t, J=7.8, 2H), 2.62-2.78 (2H), 4.08 (bs, 2H), 6.61-6.70 (3H).

Workup

  1. filtrationThe suspension was filtered though Celite
  2. washthe cake washed with MeOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9353e093489c45479dab111ef856b90e
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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